Triphenylphosphine → HCID 54451574, compound

HRID 368323Notes

Reaction equation

HRID 368323 reaction equation
[C:1]([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][OH:15])[N:10]=[CH:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O[C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[C:23](=[O:27])[CH2:22][CH2:21][CH2:20]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:4]([O:3][C:1]([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][O:15][C:17]2[CH:26]=[CH:25][C:24]3[C:23](=[O:27])[CH2:22][CH2:21][CH2:20][C:19]=3[CH:18]=2)[N:10]=[CH:9]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 46794946-Hydroxy-3,4-dihydro-1(2H)-naphthalenoneHCID 18626470HCID 18626470, compound

Product 1

HCID 54451574HCID 54451574, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-N-Boc-4-(2-hydroxyethyl)imidazole (1.06 g, 5.0 mmol), 6-hydroxytetralone (0.811 g, 5.0 mmol), and triphenylphosphine (1.44 g, 5.5 mmol) in 10 mL of freshly distilled THF was cooled in an ice bath for 10 minutes and then treated with neat diethyl azodicarboxylate (0.87 mL, 5.5 mmol) added via syringe through a rubber septum. The ice bath was permitted to melt and the reaction continued at room temperature for 5 hours. The solvent was removed in vacuo and the residue was chromatographed (silica gel, 500 g; 1:1, EtOAc:hexanes), and the pure fractions were pooled to afford 0.61 g (33%) of the title compound as a clear, colorless, viscous oil: CI-MS m/e 357 (M+ +1).

Workup

  1. additionadded via syringe through a rubber septum
  2. customThe solvent was removed in vacuo
  3. customthe residue was chromatographed (silica gel, 500 g; 1:1, EtOAc:hexanes)

Sources & evidence

ORD record
ord-df7d6b01a4fa41c485273c2615e5f16b
Source dataset
uspto-grants-2000_10
Patent number
US06133303

Reaction notes

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